Hardly a weekend goes by in the Florida Keys & Key West without a special event or festival taking place. Providing entertainment and enjoyment for visitors virtually throughout the year, the events celebrate everything from the Keys’ colorful history, artistic culture and quirky ambiance to underwater wonders, outdoor adventure and tasty cuisine.
While some selected 2017 highlights are spotlighted here, a full yearlong schedule of events throughout the Keys can be found at fla-keys.com/calendar.
The Keys’ bountiful fish and seafood harvests, culinary diversity and innovative chefs provide a focus for “taste-full” festivals throughout the island chain. Foodies can savor the flavors at events including Uncorked … the Key Largo and Islamorada Food & Wine Festival (Jan. 5-15; floridakeysuncorked.com), the Key West Food & Wine Festival (Jan. 25-29; keywestfoodandwinefestival.com) and the Original Marathon Seafood Festival (March 11-12, marathonseafoodfestival.com).
Events also abound for athletes and fans of land and sea adventures. Runners can chart a course over one of the world’s longest segmental bridges, the centerpiece of the Florida Keys Overseas Highway, during Marathon’s renowned Seven Mile Bridge Run (April 1, 7 mbrun.com). The Jewfish Creek Bridge, at the beginning of the Keys, highlights the Key Largo Bridge Run (Nov. 10-11, keylargobaptistchurch.com/key-largo-bridge-run/), while distance swimmers can test their strength in Islamorada’s 9-mile open-water Swim for Alligator Lighthouse (Sept. 23, swimalligatorlight.com).
Each July, several hundred divers and snorkelers submerge for a subsea concert celebrating the continental United States’ only living coral barrier reef. The Lower Keys Underwater Music Festival (July 8, lowerkeyschamber.com/festival.php) takes place about 6 miles off Big Pine Key in the Florida Keys National Marine Sanctuary.
Powerboat and sailing aficionados can observe internationally renowned challenges in Key West: the adrenaline-fueled Super Boat World Championship series for high-speed powerboats (Nov. 5-12, superboat.com) and the Quantum Key West Race Week sailing regatta (Jan. 15-20, keywestraceweek.com).
The life and work of legendary author Ernest Hemingway, who lived and wrote in Key West during the 1930s, are recognized during the annual Hemingway Days (July 18-23, hemingwaydays.net), while Humphrey Bogart’s films and legacy take center stage during the Humphrey Bogart Film Festival (Oct. 18-22, bogartfilmfestival.com) — held in Key Largo, where parts of the eponymous Bogie classic were filmed.
Stars of a different kind draw several hundred astronomers to the Lower Florida Keys each winter. The Winter Star Party (Feb. 20-26, scas.org/winter-star-party/) features unparalleled opportunities for viewing southern constellations, comets and celestial objects.
The island chain’s flourishing creative community also inspires annual art shows and events, including Marathon’s acclaimed Pigeon Key Art Festival (Feb. 4-5, pigeonkeyartfestival.com) that benefits the tiny Middle Keys landmark.
Costume creativity ranks high each October during Key West’s Fantasy Fest (Oct. 20-29, fantasyfest.com). The outrageous masking and costuming festival’s packed schedule culminates in a dazzling parade of large-scale floats and marching groups.
Some events are designed to appeal specifically to the Keys’ LGBT visitors, such as Key West Pride (June 7-11, keywestpride.org) and Womenfest (Sept. 6-10, womenfest.com).
And for those who want to experience the eccentric spirit of Key West, it’s embodied in the Conch Republic Independence Celebration (April 21-30, conchrepublic.com). The offbeat event commemorates the Florida Keys’ symbolic secession from the United States in 1982, and rebirth as the independent Conch Republic, to protest the establishment of a U.S. Border Patrol blockade at the head of the island chain.